Water → HCID 11992774, compound

Participants

Reaction Conditions

Reaction Steps

Compound 47 (50 mg, 0.11 mmol) was dissolved in THF (5 mL) and cooled to 0° C. under nitrogen. DIBAL (1.5 M in hexane, 500 ul, 0.33 mmol) was added drop-wise over several minutes. The ice bath was removed and the stirring reaction allowed to warm to ambient temperature. The reaction was then cooled back to 0° C. and water (10 mL) added dropwise over several minutes. The ice bath was then removed and the reaction was stirred until solids began to form. The solids were filtered and the filtrate washed several times with dichloromethane. The filtrate was concentrated in vacuuo to give 42 mg (98%) of compound 48 as a clear oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (s, 6H), 0.95 (s, 6H), 1.29 (s, 2H), 1.75 (s, 2H), 1.90 (s, 2H), 2.08-2.17 (m, 5H), 2.55 (t, J=7.3 Hz, 2H), 3.72 (t, J=6.3 Hz, 2H), 3.97 (t, J=6.1 Hz, 2H), 6.70 (d, J=9.0 Hz, 1H), 6.91-6.99 (m, 2H), 7.10-7.20 (m, 3H), 7.20-7.30 (m, 2H).

Provenance & Evidence